(1-Adamant­yl)(4-amino­phen­yl)methanol

Rouchal, M.; Nečas, M.; Vícha, R.

doi:10.1107/S1600536809012987

Volume 65
Part 5
Page o1018
May 2009

Received 23 March 2009
Accepted 6 April 2009
Online 10 April 2009

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.006 Å
R = 0.094
wR = 0.270
Data-to-parameter ratio = 13.9
Details

(1-Adamantyl)(4-aminophenyl)methanol

Michal Rouchal,^a Marek Necas ^b and Robert Vícha ^a ^*

^aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and ^bDepartment of Chemistry, Faculty of Science, Masaryk University in Brno, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
Correspondence e-mail: rvicha@ft.utb.cz

In the racemic crystal of the title compound, C₁₇H₂₃NO, enantiomers of the two crystallographically independent molecules are linked into face-to-face RSdimers via intermolecular O-HN hydrogen bonds and [pi] - [pi] interactions with centroid-centroid distances of 3.7610 (2) Å. The molecules adopt slightly different conformations and contain an adamantane cage consisting of three fused cyclohexane rings in almost ideal chair conformations, with C-C-C angles varying within the range 107.2 (4)-111.4 (4)°. In the hydrogen-bonded pair, the benzene rings are almost coplanar, the dihedral angle between them being 1.29 (13)°. The molecular packing in the crystal is stabilized by additional intermolecular N-HO hydrogen bonds.

Related literature

The title compound was prepared according to a modification of the procedure of Adkins & Billica (1948). For some important properties of adamantane-bearing compounds, see: Cromwell et al. (1985), van Bommel et al. (2001).

Experimental

Crystal data

C₁₇H₂₃NO
M_r = 257.36
Monoclinic, P 2₁ /n
a = 8.8107 (5) Å
b = 12.1593 (6) Å
c = 26.6047 (16) Å
= 93.046 (5)°
V = 2846.2 (3) Å³
Z = 8
Mo K radiation
= 0.07 mm^-1
T = 120 K
0.40 × 0.40 × 0.10 mm

Data collection

Kuma KM-4 CCD diffractometer
Absorption correction: none
20748 measured reflections
5001 independent reflections
3444 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.094
wR(F²) = 0.270
S = 1.19
5001 reflections
359 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.49 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AN1	0.84	2.06	2.890 (5)	168
O1-H1AN2	0.84	2.04	2.876 (5)	171
N1-H1BO1ⁱ	0.83 (6)	2.15 (6)	2.941 (5)	162 (5)
N2-H2BO2ⁱⁱ	0.91 (7)	2.05 (7)	2.932 (5)	163 (6)
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2796 ).

Acknowledgements

The financial support of this work by the Science Foundation of Czech Republic (grant No. 203/06/P362) and by the Czech Ministry of Education (project No. MSM 7088352101) is gratefully acknowledged.

References

Adkins, H. & Billica, H. R. (1948). J. Am. Chem. Soc. 70, 695-698.
Bommel, K. J. C. van, Metselaar, G. A., Verboom, W. & Reinhoudt, D. N. (2001). J. Org. Chem. 66, 5405-5412.
Cromwell, W. C., Bystrom, K. & Eftink, M. R. (1985). J. Phys. Chem. 89, 326-332.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds